Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!

Feb 25 – Mar 4

R2,458 ZAR per night
Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 193 reviews

Potomac River Freedom Cottage

Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.

Apr 19 – 26

R3,614 ZAR per night
Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Oct 13 – 20

R1,564 ZAR per night

Popular amenities for Leonardtown vacation rentals

Stay near Leonardtown's top sights

Leonardtown Wharf Park14 locals recommend
The Front Porch23 locals recommend
Salsas Mexican Cafe3 locals recommend
Olde Town Pub11 locals recommend
The Slice House13 locals recommend
Social12 locals recommend

Other great vacation rentals in Leonardtown

Guest favorite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 257 reviews

Bayview Bungalow

Jun 9 – 16

R2,347 ZAR per night
Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 203 reviews

Peaceful Waterfront Retreat on The Bay

Oct 22 – 29

R3,114 ZAR per night
Guest favorite

Apartment in Lexington Park

4.93 out of 5 average rating, 187 reviews

Private apartment with kitchenette

Nov 16 – 23

R1,197 ZAR per night
Guest favorite

Home in Lusby

5.0 out of 5 average rating, 110 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Oct 20 – 27

R14,151 ZAR per night
Superhost

Home in Montross

4.92 out of 5 average rating, 144 reviews

Tranquil River Home

Nov 17 – 24

R2,580 ZAR per night
Guest favorite

Guest suite in Leonardtown

4.87 out of 5 average rating, 190 reviews

Happy Guesthouse! Located waterfront

Feb 12 – 19

R2,301 ZAR per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Sep 3 – 10

R2,922 ZAR per night
Guest favorite

Apartment in Leonardtown

4.94 out of 5 average rating, 33 reviews

Retreat at Fenwick

Sep 29 – Oct 6

R2,314 ZAR per night
Guest favorite

Home in Leonardtown

4.95 out of 5 average rating, 39 reviews

Old Bay Inn

Sep 25 – Oct 2

R2,517 ZAR per night
Guest favorite

Home in Leonardtown

5.0 out of 5 average rating, 19 reviews

Water's Edge Cottage | Luxury Retreat

Sep 18 – 25

R6,665 ZAR per night
Guest favorite

Apartment in Leonardtown

4.92 out of 5 average rating, 13 reviews

Beech Creek Farm Apt

Apr 4 – 11

R2,560 ZAR per night
Superhost

Home in Leonardtown

5.0 out of 5 average rating, 10 reviews

Waterfront Cottage w/ Incredible Views

May 19 – 26

R5,894 ZAR per night

Destinations to explore